Reaction #10410

Reaction equation

3-dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione

3-Dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione

sodium hydride

Bromomethylcyclopropane

→

title compound

Yield 67.0%

3-Dibenzylamino-6,7-difluoro-1-cyclopropylmethyl-1H-quinazoline 2,4-dione

Yield 67.0%

Solvents

N,N-dimethylformamide

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is stirred at 25° C. for 18 hours
2. 2
   OtherThe reaction is quenched with 1 mL of water
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.DISSOLUTIONThe residue is dissolved in chloroform
5. 5
   Washwashed with water, brine
6. 6
   Dryingdried over magnesium sulfate
7. 7
   ConcentrationThe solution is concentrated
8. 8
   Otherpurified via chromatography (SiO2, CHCl3)

Procedure

A solution of 3-dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione (Example 16) (0.43 g, 1.1 mmol) in 10 mL of N,N-dimethylformamide is added to a suspension of sodium hydride (0.05 g, 1.3 mmol) in 10 mL of N,N-dimethylformamide and stirred for 30 minutes. Bromomethylcyclopropane (0.16 mL, 1.6 mmol) is added, and the mixture is stirred at 25° C. for 18 hours. The reaction is quenched with 1 mL of water and concentrated in vacuo. The residue is dissolved in chloroform, washed with water, brine, and dried over magnesium sulfate. The solution is concentrated and purified via chromatography (SiO2, CHCl3) to give 0.33 g of the title compound as a solid. MS CI: m/z 448 (MH+).

Source